Cyclic hydroxamic acid derivatives



United States Patent 3,531,472 CYCLIC HYDROXAMIC ACID DERIVATIVES MichioNakanishi, Oita Nakatsu, and Tadao Okada and Takauori 0e, Chikujogun,Fukuoka, Japan, assignors to gfoshitomi Pharmaceutical Industries, Ltd.,Osaka,

apan No Drawing. Filed Apr. 8, 1968, Ser. No. 719,757 Claims priority,application Japan, Apr. 8, 1967, 42/22,520 Int. Cl. C07d 93/42, 89/20,53/02 US. Cl. 260-2393 17 Claims ABSTRACT OF THE DISCLOSURE Cyclichydroxamic acid derivatives of the formula This invention relates tonovel cyclic hydroxamic acid derivatives, represented by the formula andto pharmaceutically acceptable acid addition salts thereof, wherein eachof X and X is H, halogen (e.g., Cl, F), lower alkyl, lower alkoxy, loweralkylthio or trifluoromethyl, Y is O, -S, -SO or N(R)- (R being loweralkyl), A is alkylene of two to four carbon atoms, and N(R (R is loweralkylamino, di- (lower alkyl)amino, cyclohexylamino, (phenyl-loweralkyl)amino, piperidino, morpholino, 4-lower alkyl-l-piperazinyl or4-(hydroxylower alkyl) l-piperazinyl. In the above definition lowermeans that the alkyl moiety or alkoxy moiety contains not more than 4carbon atoms. Advantageously, X and X are each H, Cl, methyl, methoxy,methylthio or trifiuoromethyl, and A is ethylene, propylene(methylethylene) or trimethylene. Examples of --N(R (R are Inethylamino,isopropylamino, dimethylamino, diethylamino, dibutylamino,cyclohexylamino, benzylamino, phenethylamino, (l-methyl-Z-phenylethyl)amino, piperidino, morpholino, 4-methyl l-piperazinyl and4-(2-hydroxyethyl)1-piperazinyl.

An advantageous subgroup of compounds according to the inventioncorrespond to the formula Patented Sept. 29, 1970 wherein X and X arethe same or different and each is H, Cl, CH CH O, CH S or CF Y is O, S-or -N(CH and N(R (R is methylarnino, isopropylamino, dimethylamino,cyclohexylamino, morpholino or 4- (2-hydroxyethyl 1-piperazinyl.

The aforedescribed compounds are prepared by reacting the appropriatehydroxamic acid of the formula Y (H) with the corresponding compound ofthe formula:

R1 X3AN/ R (III) wherein X is halogen or organic sulfonyloxy (e.g.,methylsulfonyloxy, p-tolylsulfonyloxy), :or by reacting a compound ofthe formula:

wherein X is halogen or organic sulfonyloxy, with an amine of theformula:

The reactions can be carried out in a solvent such as water, methanol,ethanol, propanol, butanol, acetone, methyl ethyl ketone, cyclohexanone,pyridine, dioxane, tetrahydrofuran, dimethylformamide, dirnethylsulfoxide or liquid ammonia, advantageously at 20 to C., andadvantageously in the presence of an acid binding agent such as sodiumhydroxide, potassium hydroxide, sodium methoxide, sodium carbonate,potassium carbonate, pyridine or triethylamine.

The starting compound of the Formula II is produced, for example, bycatalytic reduction of a compound of the formula wherein X X and Y havethe same meanings as defined above and R is lower alkyl, in the presenceof hydrogen and Raney nickel, whereby hydrogenation and simultaneouscyclization take place. Specific example is given as follows:

Metallic sodium (15 grams) is dissolved in 2 liters of ethanol. Ethyl o(o-nitrophenylthio benzoate 194 grams) and 10 grams of Raney nickel areadded. Hydrogenation cyclization is carried out at 10 to 15 C. underatmosspheric pressure until 28 liters of hydrogen gas is absorbed. Thereaction mixture is then allowed to stand overnight. The Raney nickel isfiltered off, and the ethanol is distilled off. The remaining sodiumsalt is dissolved in a large amount of water, and the solution isacidified with hydrochloric acid to precipitate10-hydr0xy-l0,11-dihydrodibenzo[b,f][1,4]tl1iazepin-1l-one. Afterrecrystallization from methanol it melts at 152 to 153 C.

Other starting compounds (II) are analogously prepared.

The starting compound of the Formula II is produced, for example, byreacting the compound (II) produced as above with a compound of theformula HO-A-halogen or halogenA-halogen 3 wherein A has the samemeaning as defined above and, upon necessity, esterifying the resultantproduct with an organic sulfonyl chloride. Specific example is given asfollows:

10 hydroxy-10,1l-dihydrodibenzoljbjj [l,4]thiazepinll-one (24 grams) isdissolved in 100 milliliters of dimethylformamide. Potassium carbonate(18 grams) and ethylene bromide (75 grams) are added, and the reactionis carried out at 40 C. for 3 hours. The reaction mixture is poured intoa large amount of ice water. An oil layer formed is taken up withmethylene chloride. The extract layer is dried over sodium sulfate.After removal of volatile matter by distillation and recrystallizationfrom hexane, there is obtained 22.5 grams of 10-(2-bromoethoxy) 10,11dihydrodibenzo[b,f][l,4]thiazepin 11 one melting at 94 to 96 C.

Other starting compounds (II) are analogously prepared.

The compounds of Formula I can be converted in per se conventionalmanner into acid addition salts with inorganic acids (e.g.,hydrochloric, hydrobromic and sulfuric acids, etc.) or organic acids(e.g., oxalic, maleic, fumaric, tartaric, citric ando-(p-hydroxybenzoyl)benzoic acids, etc.).

The compounds of Formula I and pharmaceutically acceptable acid additionsalts thereof have histamine-, acetylcholineand reserpine-antagonizingactivities as shown, for example, by the following tests:

The test for histamine antagonistic activity was made according to themethod described by J. M. van Rossum et al. in Archives Internationalesde Pharmacodynamie et de Therapie, vol. 143, pages 240246 and 299330(1963) and the test for reserpine antagonistic activity was performedessentially in accordance with the method described by R. Fielden et al.in Methods in Drug Evaluation, pages 149-157 (North-Holland PublishingCompany, Amsterdam, 1966; editors: P. Mantegazza and F. Piccinini). pAis the negative of the logarithm, to the base 10, of the molarconcentration of the test compound which reduces the effect of twicedose of histamine on contracting action of the guinea pig intestine invivo to that of a single dose; RD is the subcutaneous dose of the testcompound which prevents ptosis caused by the administration of reserpinein 20% of the animals.

Reserpine antagonistic activity, RDzo (mouse),

Histamine antagonistic mg./kg.

activity, pA2

Test compund" Owing to the remarkable pharmaceutical activities and lowtoxicity, the compounds of the invention are useful as antiallergicagents or antidepressants in the form of pharmaceutical compositions inadmixture with a suitable and conventional carrier or adjuvant,administrable orally or by way of injection, without giving harm to thehost.

The pharmaceutical compositions may take the form of tablets, granules,powders, syrups or injectable solutions, and may be administered orallyor parenterally, usual daily doses lying in the range of 25 to 300milligrams per human adult. These compositions are especially useful inthe relief of depressant conditions and, more especially in thetreatment of allergic conditions, specifically urticaria, eczema,allergic rhinitis, asthma and hay fever.

The numbering of the positions according to the present invention isshown as follows:

EXAMPLE 1 10 hydroxy 10,11 dihydrodibenzo[b,f][1,4]thiazepin-ll-one (24grams) is dissolved in 1 00 milliliters of dimethylformamide, 15 gramsof potassium carbonate and 17 grams of Z-dimethylaminoethylmethanesulfonate are added, and the reaction is carried out at to C. for4 hours. The mixture is then poured into a large amount of ice water.The oil separated is taken up with benzene, the benzene layer isextracted with hydrochloric acid, and the aqueous extract layer is madealkaline with sodium hydroxide. The oil separated is taken up withbenzene and dried over sodium sulfate. After removal of the benzene bydistillation, the residue, which solidifies on standing, isrecrystallized from a mixture of hexane and benzene to give10(2-dimethylaminoethoxy) 10,11 dihydrodibenzo [b,f][1,4]thiazepinll-onein yield. It melts at 119 to 120 C., and its acid maleate at to 131 C.

EXAMPLE 2 10 hydroxy 10,11 dihydrodibenzo[b,f] [l,4]oxazepin-ll-one (1.9grams) is dissolved in 10 milliliters of dimethylformamide, and 2.5grams of potassium carbonate and 1.5 grams of Z-dimethylaminoethylchloride are added. The reaction is carried out at 40 to 45 C. for 4hours. The reaction mixture is treated as in Example 1 to give10-(Z-dimethylaminoethoxy)-10,11-dihydrodibenzo[b,f][1,4]0xazepin-l1-one in 75.3% yield. It occurs as anoil, and its acid maleate melts at 113 to 114 C.

EXAMPLE 3 l0 hydroxy 10,11dihydrodibenzo[b,f][1,4]thiazepin-l1-one-5,5-dioxide (5.5 grams) isdissolved in 30 milliliters of dimethylformamide, and 6.2 grams ofpotassium carbonate and 3.5 grams of Z-dimethylaminoethyl chloride areadded. The reaction is carried out at 50 C. for 4 hours. The reactionmixture is treated as in Example 1 to give10-(Z-dimethylaminoethoxy)-10, 11 dihydrodibenzo[b,f][1,4]thiazepin 11one 5,5 dioxide in 80% yield. It occurs as an oil, and its acid maleatemelts at 157 to 158 C.

EXAMPLE 4 10 hydroxy 10,11 dihydrodibenzo[b,f][1,4]thiazepin-ll-one (9.8grams) is dissolved in 75 milliliters of dimethylformamide, and 4.5grams of sodium methoxide and 6.5 grams of 3-dimethylaminopropylchloride are added. The reaction is carried out at 50 to 60 C. for 4hours. The reaction mixture is treated as in Example 1 to give-(B-dimethylaminopropoxy)-l0,1l-dihydrodibenzo[b,f][l,4]thiazepin-ll-onein 78.5% yield. It melts at 72 to 73 C., and its acid maleate melts at124 to 125 C.

EXAMPLES 5 to Other examples of compounds (I) which can be produced froma cyclic hydroxamic acid and an aminoalkyl halide in 63% to 92% yield ina manner similar to that described in Example 4 are:

10 (2 diethylaminoethoxy) 10,11 dihydrodibenzo[b,f][1,4]thiazepin-l1-one, its hydrochloride melting at 179 to 180 C.,

1O (2 dimethylaminopropoxy) 10,11 dihydrodibenzo[b,f][l,4]thiazepin 11one, its acid maleate melting at 170 to 172 C.,

8 chloro 10 (2 dimethylaminoethoxy) 10,11dihydrodibenzo[b,f][1,4]thiazepin-11-one, its acid maleate melting at149 to 150 C.,

10 (2 dimethylaminoethoxy) 8 methyl 10,11dihydrodibenzo[b,f][1,4]thiazepin-l1-one, its acid maleate melting at153 to 154 C.,

10 (2 dimethylaminoethoxy) 8 methylthio 10,11-

dihydrodibenzo[b,f][l,4]thiazepin-l1-one melting at 97 to 98 C., itsacid maleate melting at 164 to 165 C.,

10 (2 dimethylaminoethoxy) 8 trifiuoromethyl 10, 11-dihydrodibenzo[b,f][1,4]thiazepin-11-one, its acid maleate melting at 165 to 166 C.,

7 chloro 10 (2 dimethylaminoethoxy) 10,11dihydrodibenzo[b,f][1,4]thiazepin-1l-one, its acid maleate melting at149 C.,

10 (2 dimethylaminoethoxy) 7 methoxy 10,11- dihydrodibenzo[b,f][1,4]thiazepin-11-one, its acid maleate melting at 147 to 148 C.,

10 (3 piperidinopropoxy) 10,11 dihydrodibenzo [b,f][l,4]thiazepin-11-onemelting at 72 to 74 C., its acid maleate melting at 171 to 172 C.,

2,7 dichloro 10 (2 dime'thylaminoethoxy) 10,11- dihydrodibenzo[b,f][l,4]thiazepin-11-one, its acid maleate melting at 140 C., and

10 (2 cyclohexylaminoethoxy) 10,11 dihydrodibenzo[b,f][l,4]thiazepin-11-one, its acid oxalate melting at 200 0.

EXAMPLE 16 A mixture of 7 grams of 10-(2-bromoethoxy)-10,11-dihydrodibenzo[b,f] [1,4]thiazepin-1l-one, 5- grams of morpholine, 0.5gram of potassium iodide and 70 milliliters of ethanol are heated at 50C. for 3 hours. Then the ethanol is distilled off, and 50 milliliters ofdilute hydrochloric acid is added to the residue. The unreacted 10 (2bromoethoxy) 10,11 dihydrodibenzo[b,f] [l,4]thiazepin-l1-one is removedby extraction with benzene. The aqueous layer is made alkaline withsodium hydroxide, the separated oil is extracted with benzene, theextract is washed with water, and the benzene is then distilled off. Theremaining crude product is recrystallized from a mixture of hexane andethyl acetate to give 10 (2 morpholinoethoxy) 10,11 dihydrodibenzo[b.f][l,4]thiazepin-11-one melting at 90 to 91 C. in 72% yield. Its acidfumarate melts at 161 to 162 C.

EXAMPLES 17 TO 23 Other examples of compounds (I) which can be producedfrom a 10-(haloalkoxy)-10,11-dihydrodibenzo[b,f] [1,4]thiazepin-ll-oneand an amine in a manner similar to that described in Example 16 in 52to 79% yield are:

10 (2 piperidinoethoxy) 10,11 dihydrodibenzo[b,f] [1,4]-thiazepin-l1-onemelting at 109 to 110 C., its acid fumarate melting at 159 to 160 C.,

10-[2 (4 methyl-l-piperazinyl)ethoxy]-l0,ll-dihydrodibenzo[b,f][1,4]thiazepin-11-one melting at 100 to 101 C., its dihydrochloridemelting at 210 to 212 C.,

l0-{2-[4-(2-hydroxyethyl)-1-piperazinyl]ethoxy} 10,11-

6 dihydrodibenzo[b,f] [1,4]thiazepin-1l-one, its dihydrochloride meltingat 210 C., 10-(2-isopropylaminoethoxy)-10,11 dihydrodibenzo[b,f][1,4]thiazepin-11-one, its acid maleate melting at 159 to 160 C.,l0-(2-methylaminoethoxy) 10,11 dihydrodibenzo[b,f][1,4]thiazepin-l1-one, its acid maleate melting at 177 to 178 C., and10-[2-(1-methyl-2-phenylethylamino)ethoxy] 10,11 dihydrodibenzo[b,f][1,4]thiazepin-11-one, its hydrochloride melting at 160 to 162 C.10-(2-methylaminoethoxy) 10,11 dihydrodibenzo[b,f] [l,4]oxazepin-11-oneis also prepared similarly, its acid maleate melting at 163 to 164 C.

EXAMPLE 24 10-hydroxy-5-methyl-10,11-dihydro 5H dibenzo[b,e][l,4]diazepin-11-one (4.8 grams, M.P. 181-183 C.) is dissolved in 40milliliters of dimethylformamide, and 1.4 grams of sodium ethoxide isadded. The mixture is stirred at 40 to 45 C. for 30 minutes. To thissolution is added 2.5 grams of Z-dimethylaminoethyl chloride, and thewhole is heated at 50 C. to 55 C. for 4 hours. Then it is poured into alarge amount of water. The oil separated is taken up with toluene, thetoluene layer is extracted with 10% hydrochloric acid, the aqueousextract layer is made alkaline with aqueous ammonia, the separated oilis taken up with chloroform, and the extract layer is washed with water,dried over sodium sulfate and concentrated. The residual oil (6 grams)is dissolved in isopropanol and treated with oxalic acid to give10-(2-dimethylaminoethoxy)-5-methyl-10,1l-dihydro 5H dibenzo[b,e] [1,4]diazepin-ll-one hydrogen oxalate melting at 166.5 C.

EXAMPLE 25 10-hydroxy-5-methyl-l0,ll-dihydro 5H dibenzo[b,e][1,4]diazepin-11-one (4.8 grams) is dissolved in 70 milliliters ofdioxane, 1.4 grams of sodium ethoxide is added, and the mixture isstirred at 40 to 45 C. for 2 hours. To this solution is added 5.2 gramsof 3-dimethylaminopropyl p-toluenesulfonate. Then reaction is carriedout at 55 to 60 C. for 6 hours. The reaction mixture is treated as inExample 24 to give an oil (5.4 grams), which is dissolved in isopropanoland treated with fumaric acid. There is obtained 5.8 grams ofl0-(3-dimethylaminopropoxy)-5-methyl-10,1l-dihydro 5H dibenzo]b,e][1,4]diazepin-ll-one hydrogen fumarate melting at 143 to C.

EXAMPLE 26 7-chloro-10-hydroxy-5-methyl-10,11 dihydroSH-dibenzo[b,e][1,4]diazepin-11-one (5.5 grams, M.P. 173.5- 174.5 C.) isdissolved in 50 milliliters of dimethylformamide, 1.4 grams of sodiumethoxide is added, and the mixture is stirred at 40 to 45 C. for 30minutes. To this solution is added 2.5 grams of Z-dimethylaminoethylchloride, and the whole is heated at 50 to 55 C. for 4 hours and thentreated as in Example 24. The remaining oil is crystallized from ligrointo give 5.6 grams of 7- chloro-10-(2-dimethylaminoethoxy) 5 methyl10,11- dihydro-SH-dibenzo[b,e] [1,4]diazepin-11-one melting at 115 C.Its acid fumarate obtained by treatment with fumaric acid in isopropanolmelts at to 161 C.

EXAMPLE 27 10-hydroxy-5-methyl-10,1l-dihydro 5H bibenzo[b,e][1.4]diazepin-11-one (4.8 grams) is dissolved in 40 milliliters ofdioxane, 1.1 grams of sodium methoxide is added, and the mixture isstirred at 50 to 55 C. for 30 minutes. To this solution is added 7.5grams of ethylene bromide and the whole is kept at 50 to 55 C. for 4hours. The reaction mixture is poured into a large amount of water, theoil separated is taken up with chloroform, and the chloroform layer iswashed with Water, dried over sodium sulfate and concentrated.10-(2-bromoethoxy)-5-methyl-10,1l-dihydro-SH-dibenzo[b,e][1,4]diazepin-11-one is obtained as a viscous oil (6.8 grams).

This is dissolved in 40 milliliters of ethanol, 4 grams ofisopropylamine is added, and the whole is kept at 50 to 55 C. for 6hours. The reaction mixture is poured into water, the separated oil istaken up with toluene, the toluene layer is extracted with 10%hydrochloric acid and the extract is made alkaline with aqueous ammonia.The oil separated is taken up with chloroform, washed with water andconcentrated. Crystallization of the residual oil from hexane gives 4grams of 10-(2-isopropylaminoethoxy)-5- methyl-10,1l-dihydro-5Hdibenzo[b,e] [1,4]diazepin-11- one melting at 87 C. Its acid oxalatemelts at 167 C.

EMMPLE 28 In a manner similar to that described in Example 27, 7 gramsof 10-(2-brom0ethoxy)-5-methyl-10,1l-dihydro- 5H-dibenzo[b,e][1,4]diazepin-11-one and 3 grams of phenethylamine are allowed to reactin 40 milliliters of ethanol in the presence of 4.5 grams oftriethylamine and 0.3 gram of potassium iodide and the reaction mixtureis treated similarly as in Example 27 to give 4.5 grams of 5-methyl-10-(2-phenethylaminoethoxy)-10,11 dihydro-SH-dibenzo[b,e][1,4]diazepin-1l-one. Its acid oxalate melts at 156 to 157C.

EXAMPLES 29 TO 37 The following compounds (I), for example, aresimilarly prepared:

5-rnethyl-10-[3-(4-methyl-1-piperazinyl)propoxy] 10,11-

dihydro-5H-dibenzo[b,e] [1,4]diazepin-11 one melting at 102 C., itshydrochloride melting at 208 C.,

10-(2-dimethylaminoethoxy)-5-methyl-8-trifiuoromethyl-10,1l-dihydro-SH-dibenzo[b,e] 1,4]diazepin-11-one, its acid oxalatemelting at 179 C.,

5-methyl-10-(2-morpholinoethoxy)-10,1 l-dihydro-SH- dibenzo[b,e][l,4]diazepin-ll-one melting at 130 C., its acid maleate melting at130.5 to 132 C.,

S-methyl-l-(2-piperidinoethoxy)-10,1l-dihydro-SH- dibenzo[b,e][1,4]diazepin-11-one, its acid oxalate melting at 156 C.,

2,7-dichloro-1O (2-dimethylaminoethoxy) --methyl10,1l-dihydro-SH-dibenzo[b,e] [1,4]diazepin-l1-one melting at 126 to 127C., its acid fumarate melting at 172 to l73.5 C.,

lO-(Z-dimethylaminoethoxy)-5-methyl-8-methylthio-10,1l-dihydro-SH-dibenzo[b,e] [1,4] diazepin-l l-one melting at 95 to 97C.,

S-methyl--(2-methylaminoethoxy)-10,1 l-dihydro-SH- dibenzo[b,e][1,4]diazepin-1l-one, its acid fumarate melting at 127 to 129 C.,

10-(2-dibutylaminoethoxy)-5-methyl-10,1 l-dihydro-SH- dibenz0[b,e][1,4]diazepin-l1-one, its acid oxalate melting at 127 to 129 C. withdecomposition, and

10- (2-cyclohexylaminoethoxy) -5-methyl-10,1 l-dihydro- 5H-dibenzo[b,e][1,4]diazepin-1l-one melting at 124 to 126 C., its acid oxalate meltingat 174 to 175 C. What is claimed is:

1. A compound of the formula wherein X and X are the same or differentand each is NR )R is lower alkylamino, di(lower alkyl)amino,trifiuoromethyl, Y is O, S-, SO or N(R)- (R being lower alkyl), A is Calkylene, and NR )(R is lower alkylamino, di(lower alkyl)amino,cyclohexylamino, (phenyl-lower alkyl)amino, piperidino,

wherein X and X are the same or diiferent and each is H, Cl, CH CH O, CHS or CF Y is -O, S- or N(CH and N(R )(R is methylamino, isopropylamino,dimethylamino, cyclohexylamino, morpholino or 4- (2-hydroxyethyl-1-piperazinyl.

4. A pharmaceutically acceptable acid addition salt of a compoundaccording to claim 3.

5. A compound according to claim 3, said compound being 10-(Z-dimethylaminoethoxy)-10,l l-dihydl'odibenzo [b,f][1,4]thiazepin-11-one.

6. A compound according to claim 3, said compound being10-(Z-dimethylarninoethoxy)-10,1 l-dihydrodibenzo [b,f][1,4]oxazepin-11-one.

7. A compound according to claim 3, said compound being8-chloro-10-(Z-dimethylaminoethoxy)-10,1 l-dihydrodibenzo [b,f][1,4]thiazepin-11-one.

8. A compound acocrding to claim 3, said compound being 10-(Z-dimethylaminoethoxy) -8-methyl-10,1 l-dihydrodibenzo [b,f][1,4]thiazepin-l1-one.

9. A compound according to claim 3, said compound being10-(Z-dimethylaminoethoxy)-8methylthio-10,1l-dihydrodibenzo [b,f] 1,4]thiazepin-l l-one.

10. A compound according to claim 3, said compound being7-chloro-10-(Z-dimethylaminoethoxy)-10,1l-dihydrodibenzo[b,f][1,4]thiazepin-11-one.

11. A compound according to claim 3, said compound being 10-{2-[4-(2-hydroxyethyl) -1-piperazinyl]ethoxy} 10,

11-dihydrodibenzo[b,f] [1,4]thiazepin-11-one.

12. A compound according to claim 3, said compound being7-chloro-10-(Z-dimethylaminoethoxy)-5-methyl-l0, 1l-dihydro-SH-dibenzo[b,e] [1,4] diazepin-l l-one.

13. A compound according to claim 3, said compound being 10-2-dimethyl-aminoethox'y') -5-methyl-8-trifluoromethyl10,1l-dihydro-SH-dibenzo[b,e] [l,4]diazepin-1lone.

14. A compound according to claim 3, said compound beingS-methyl-IO-(2-morpholinoethoxy)-10,1l-dihydro- SH-dibenzo [b,e][1,4]diazepin-11-one.

15. A compound according to claim 3, said compound being 10-2-isopropylaminoethoxy -5rnethyl- 10,1 l-dihydro-SH-dibenzo [b,e][1,4]diazepin-11-one.

16. A compound according to claim 3, said compound being 10-(2-cyclohexylaminoethoxy)-5-methyll 0,1 1-dihydro-SH-dibenzo [b,e][1,4]diazepin-11-one.

17. A compound according to claim 3, said compound being5-methyl-10-(2-methylaminoethoxy)-10,1l-dihydro- SH-dibenzo [b,e][1,4]diazepin-11-one.

References Cited UNITED STATES PATENTS 3,419,547 12/1968 Schmutz et al260239.3

HENRY R. JILES, Primary Examiner R. T. BOND, Assistant Examiner U.S. Cl.X.R.

